WO2013050311A1 - Compositions de résine époxy contenant un dérivé de 2-oxo-[1,3]dioxolane - Google Patents

Compositions de résine époxy contenant un dérivé de 2-oxo-[1,3]dioxolane Download PDF

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Publication number
WO2013050311A1
WO2013050311A1 PCT/EP2012/069304 EP2012069304W WO2013050311A1 WO 2013050311 A1 WO2013050311 A1 WO 2013050311A1 EP 2012069304 W EP2012069304 W EP 2012069304W WO 2013050311 A1 WO2013050311 A1 WO 2013050311A1
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WO
WIPO (PCT)
Prior art keywords
epoxy resin
groups
resin compositions
formula
amino
Prior art date
Application number
PCT/EP2012/069304
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German (de)
English (en)
Inventor
Rainer Klopsch
Miran Yu
Original Assignee
Basf Se
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Basf Se filed Critical Basf Se
Priority to EP12769403.2A priority Critical patent/EP2764033B1/fr
Priority to DK12769403.2T priority patent/DK2764033T3/en
Publication of WO2013050311A1 publication Critical patent/WO2013050311A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
    • C08G59/42—Polycarboxylic acids; Anhydrides, halides or low molecular weight esters thereof
    • C08G59/4284—Polycarboxylic acids; Anhydrides, halides or low molecular weight esters thereof together with other curing agents
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
    • C08G59/50—Amines

Definitions

  • Epoxy Resin Compositions Containing a 2-Oxo [1,3] Dioxolane Derivative Description The present application includes by reference the US Provisional Application 61/542828 filed on 04.10.201 1.
  • the invention relates to epoxy resin compositions containing a) epoxy resins and
  • Epoxy resins also called epoxy resins
  • oligomeric compounds having on average more than one epoxide group per molecule. These can be converted into thermosets by reaction with suitable hardeners or by polymerization of the epoxide groups.
  • Cured epoxy resins due to their excellent mechanical and chemical properties, such as high impact strength, high abrasion resistance, good chemical resistance, in particular a high resistance to alkalis, acids, oils and organic solvents, high weather resistance, excellent adhesion to many materials and high electrical insulation capacity, widespread.
  • Suitable hardeners are compounds having at least two functional groups which can react with the epoxide groups (also called oxirane groups) and / or hydroxyl groups of the epoxy resin prepolymers to form covalent bonds, eg.
  • epoxide groups also called oxirane groups
  • hydroxyl groups As compounds with amino groups, hydroxy groups and carboxyl groups or derivatives thereof, such as anhydrides. Accordingly, aliphatic and aromatic polyamines, carboxylic anhydrides, polyamidoamines, aminoplasts or phenoplasts are usually used as hardeners for epoxy resins.
  • Reactive diluents are solvents which have functional groups which react with the epoxide groups of the resin and / or the functional groups of the curing agent to form covalent bonds, which may be e.g. B. compounds, which in turn contain oxirane groups.
  • Reactive diluents are, in particular, glycidyl ethers of polyfunctional aliphatic alcohols such as 1,4-butanediol diglycidyl ether, 1,6-hexanediol diglycidyl ether, diethylene glycol diglycidyl ether or glycidyl ether of trimethylolpropane.
  • monofunctional reactive diluents are also suitable, examples are z. C12 to C14 fatty alcohol glycidyl ether.
  • Epoxy resins Suitable epoxy resins are, in particular, those which are customarily used in curable epoxy resin compositions. Particular mention may be made of compounds having from 1 to 10 epoxide groups, preferably having at least two epoxide groups in the molecule. The content of epoxide groups in typical epoxy resins is in the range from 120 to 3000 g / equivalent, calculated as so-called epoxide equivalent according to DIN 16945.
  • the epoxy resins may be liquid resins, solid resins or mixtures thereof. Liquid resins differ from solid resins in their lower viscosity. In addition, liquid resins generally have a higher proportion of epoxide groups and, accordingly, a lower epoxide equivalent.
  • the content of epoxide groups in typical liquid resins is usually in the range of 120 to 200 g / equivalent and that of the solid resins in the range of 450-3000 g / equivalent, calculated as so-called epoxide equivalent according to DIN 16945.
  • the viscosity of the liquid resins is usually in the range from 1 to 20 Pas, preferably in the range from 5 to 15 Pas, at 25 ° C.
  • the viscosity of the solid resins is usually in the range from 5 to 40 Pas, preferably in the range from 20 to 40 Pas, at 25 ° C.
  • the viscosities stated here are the values determined in accordance with DIN 53015 at 25 ° C. as 40% strength solutions of the resins in methyl ethyl ketone.
  • Suitable epoxy resins are, for example, commercially available under the trade names EPILOX®, EPONEX®, EPIKOTE®, EPONOL®, D.E.R, ARALDIT® or ARACAST®.
  • the epoxy resin is selected from polyglycidyl ethers of aromatic polyols.
  • the parameter n indicates the number of repeating units, the mean value of n corresponding to the respective average molecular weight.
  • epoxy resins based on polyglycidyl ethers of aromatic polyols are also glycidyl ethers of phenol- and cresol-based novolacs.
  • Novolacs are produced by the acid-catalyzed condensation of formaldehyde and phenol or cresol. Reaction of the novolaks with epichlorohydrin gives the glycidyl ethers of novolacs.
  • Insbeondere Also suitable are mixtures of different polyglycidyl ethers of aromatic polyols.
  • Epoxide resins for coating formulations also include polyacrylate resins containing epoxide groups.
  • ethylenically unsaturated monomer which contains at least one epoxide group, in particular in the form of a glycidyl ether group, in the molecule with at least one further ethylenically unsaturated monomer which does not contain an epoxide group in the molecule, preferably at least one of the comonomers is an ester of acrylic acid or methacrylic acid.
  • the ethylenically unsaturated monomers containing at least one epoxide group in the molecule are glycidyl acrylate, glycidyl methacrylate and allyl glycidyl ether.
  • Examples of ethylenically unsaturated monomers which do not contain an epoxide group in the molecule are alkyl esters of acrylic and methacrylic acid containing 1 to 20 carbon atoms in the alkyl radical, in particular methyl acrylate, methyl methacrylate, ethyl acrylate, ethyl methacrylate, butyl acrylate, butyl methacrylate, 2-ethylhexyl acrylate and 2-ethylhexyl.
  • Further examples of ethylenically unsaturated monomers which contain no epoxide groups in the molecule are acids, such as. For example, acrylic acid and methacrylic acid. Acid amides, such as.
  • acrylic acid and methacrylamide vinyl aromatic compounds such as styrene, methyl styrene and vinyl toluene, nitriles such as acrylonitrile and methacrylonitrile, vinyl and vinylidene halides such as vinyl chloride and vinylidene fluoride, vinyl esters such.
  • the epoxide group-containing polyacrylate resin usually has an epoxide equivalent weight of from 400 to 2500, preferably from 500 to 1500, particularly preferably from 600 to 1200.
  • the number average molecular weight (determined by gel permeation chromatography using a polystyrene standard) is typically in the range from 1000 to 15,000, preferably from 1200 to 7000, particularly preferably from 1500 to 5000.
  • the glass transition temperature (TG) is typically in the range from 30 to 80 ° C, preferably from 40 to 70 ° C, more preferably from 50 to 70 ° C (measured by differential scanning calorimetry (DSC)).
  • DSC differential scanning calorimetry
  • the epoxy resins can also be derived from other epoxides (non-glycidyl ether epoxy resins). These include, in particular, compounds, including oligomers and polymers, which have at least one, in particular a plurality of epoxidized cycloaliphatic groups, in particular 7-oxabicyclo [4.1.0] heptyl groups, which are obtainable by epoxidation of compounds having cyclohexenyl groups. Examples of the epoxidation products of compounds having at least one cycloolefinic group are 4-epoxyethyl-1,2-epoxycyclohexane and the compound of the following formula:
  • the above epoxy resins may each be used as the sole epoxy resins or as a mixture.
  • the epoxy resin compositions contain a 2-oxo [1, 3] dioxolane derivative of the formula I.
  • radicals R 1 to R 4 are an electron-withdrawing organic group having 1 to 20 C atoms or an electron-withdrawing heteroatom and the remaining radicals R 1 to R 4 independently of one another represent an H atom or a hydrocarbon group having 1 to 20 C atoms stand.
  • radicals R 1 and R 4 or only R 1 represent an electron-withdrawing organic group having 1 to 20 C atoms or electron-withdrawing heteroatom.
  • radicals R 1 and R 4 or only R 1 represent an electron-withdrawing organic group having 1 to 20 C atoms or electron-withdrawing heteroatom.
  • only radical R 1 is an electron-withdrawing organic group having 1 to 20 C atoms or an electron-withdrawing heteroatom.
  • the remaining radicals R 1 to R 4 are preferably, independently of one another, an H atom or a C 1 to C 10, in particular a C 1 to C 4, alkyl group; particularly preferably, the remaining radicals R 1 to R 4 are an H atom.
  • R5 is a hydrocarbon radical having 1 to 20 carbon atoms, which may optionally be substituted by one or more functional groups selected from carboxylic acid groups, carboxylic acid ester groups or hydroxyl groups and the two radicals R6 in the amide group independently of one another for an H atom or stand a residue R5.
  • R5 in the above formulas z Example by a carboxylic acid group, by one or two hydroxyl groups or by both a carboxylic acid group and one or two hydroxyl groups.
  • R 5 is in each case an unsubstituted, aliphatic, cycloaliphatic or aromatic hydrocarbon radical having 1 to 10 C atoms.
  • R5 is a C1 to C10 alkyl group, in particular a C1 to C4 alkyl group, for. As an ethyl group or especially a methyl group.
  • the electron-withdrawing organic group or the electron-withdrawing heteroatom is a fluorine atom, a nitrile group, an ester group of the formula or an amide group of the formula
  • the electron-withdrawing organic group is an ester group of the formula
  • the compound of the formula I is a 2-oxo [1,3] dioxolane-4-carboxylic acid ester of the formula IIa
  • R5 has the above meaning.
  • R 5 is a C 1 - to C 4 -alkyl radical, in particular a methyl or ethyl radical, very particularly preferably a methyl radical.
  • 2-Oxo [1, 3] dioxolane derivatives can be prepared in a known manner from the corresponding epoxides by addition of carbon dioxide (CO2).
  • 2-Oxo [1, 3] dioxolane derivatives can also be prepared by reacting diols in which adjacent carbon atoms are substituted by hydroxyl groups, with dialkyl carbonates with elimination of alkanols, preferably with dimethyl carbonate with elimination of methanol or by reaction with phosgene (COC) with elimination be prepared by HCl.
  • 2-oxo [1, 3] dioxolane derivatives of the formula IIb are obtainable by reaction of tartaric diesters, the two ester groups corresponding to the radical R5, with phosgene.
  • the compound (s) of the formula I in a total amount of at least 0.1 parts by weight, often at least 0.5 parts by weight, especially at least 1 parts by weight, especially at least 2 or at least 5 parts by weight based on 100 parts by weight of the epoxy resins , use.
  • the compound (s) of the formula I will be used in a total amount of at most 100 parts by weight, preferably at most 70 parts by weight, especially at most 50 parts by weight, based on 100 parts by weight of the epoxy resins.
  • the epoxy resin compositions therefore contain compounds of the formula I in amounts of, for. B.
  • the epoxy resin compositions may also contain conventional reactive diluents.
  • This is especially understood as low molecular weight compounds having a molecular weight of preferably at most 250 daltons, z.
  • the oxirane groups preferably glycidyl groups, e.g. In the form of glycidyl ether groups, glycidyl ester groups or glycidyl amide groups.
  • the epoxide functionality, ie the number of epoxide groups per molecule, in the case of the reactive diluents is typically in the range from 1 to 3, in particular in the case of rich from 1, 2 to 2.5.
  • glycidyl ethers of aliphatic or cycloaliphatic alcohols which preferably have 1, 2, 3 or 4 OH groups and 2 to 20 or 4 to 20 C atoms
  • glycidyl ethers of aliphatic polyetherols containing 4 to 20 C atoms exhibit. Examples for this are:
  • Glycidyl ethers of saturated alkanols having 2 to 20 carbon atoms such as, for example, C 2 -C 20 -alkyl glycidyl ethers, such as 2-ethylhexyl glycidyl ether, or C 12 -C alkyl-alkyl glucidyl ethers;
  • Preferred aromatic co-hardeners are, for. B. also by one to three aminomethylene (H2N-CH2-) substituted benzene.
  • H2N-CH2- aminomethylene substituted benzene
  • it is benzene, which by two H2N-CH2 groups is substituted at any position of the benzene ring, for example, xylenediamine having the formula
  • Preferred cycloaliphatic co-hardeners are, for example, also cyclohexane substituted by one to three aminomethylene groups (H 2 N-CH 2 -).
  • it is cyclohexane, which is substituted by two H2N-CH2 groups at any position of the benzene ring.
  • Such amino hardeners H2 are e.g. Polyamidoamines, phenalkamines, epoxy-amine adducts, polyetheramines or other amino compounds other than the amino hardeners H1 (co-curing agents) or mixtures thereof.
  • radicals R.sup.1, R.sup.12 and R.sup.13 are preferably a hydrocarbon group having 1 to 10 carbon atoms which is substituted by a hydroxyl group.
  • the compound of formula IV acts as a catalyst (accelerator). It can be added separately or together with the amino hardeners of the epoxy resin composition.
  • the compound of the formula IV may preferably be used in amounts of from 0.1 to 30% by weight, more preferably in amounts of from 0.5 to 20% by weight, based on epoxy resins a).
  • the two-component epoxy resin composition therefore comprises a separate epoxy resin composition containing epoxy resins, compounds of formula I and optionally other ingredients, but no hardener, in particular no amino hardener, and a separate hardener mixture containing hardener, preferably amino hardener, but no epoxy resins.
  • the hardener mixture particularly preferably contains a mixture of amino hardeners H1 and H2 and optionally further constituents, eg. B. also an accelerator of the formula IV, as stated above.
  • the cure z. B. also be microwave induced.
  • the curing is carried out at -10 to 80 ° C and in a particularly preferred embodiment at -10 to 40 ° C or at -10 to 20 ° C. It is advantageous that the curing can take place under normal ambient conditions such as room temperature and / or exposure to sunlight.
  • the epoxy resin compositions can be used in a variety of ways. They are suitable, for example, as a binder component in coating or impregnating agents, as adhesives, for the production of composite materials, in particular those based on carbon fiber materials or glass fiber materials, for the production of moldings or as casting compounds, in particular as casting compounds for embedding, bonding or solidification of moldings.
  • This and the following explanations apply to both the 1K and 2K systems, with preferred systems being the 2K systems for all of the above uses.
  • the epoxy resin compositions Since the reactivity of the epoxy resin compositions is comparatively high, curing at low temperatures, e.g. B. in the range of 0 to 50 ° C and in particular in the range of 5 to 35 ° C.
  • the epoxy resin compositions are also useful as insulating coatings in electronic applications, e.g. B. as an insulating coating for wires and cables. Also mentioned is the use for the production of photoresists. They are particularly suitable as a refinish, z. Also, when repairing pipes without dismantling the pipes (your in-place pipe (CIPP) rehabilitation). They are also suitable for sealing or coating of floors.
  • CIPP your in-place pipe
  • the epoxy resin compositions are especially suitable for the production of composite materials.
  • composites are different materials, eg. For example, plastics and reinforcing materials (fibers, carbon fibers) are joined together by the cured epoxy resin.
  • Epoxy resin 1 Epoxy resin 1:
  • IPDA Isophorone diamine
  • the cap at the funnel outlet is opened and the funnel is moved horizontally at a constant speed (1 cm / h or 10 cm / h) in the direction of the pressure rollers.
  • a sand trace and two pressure traces parallel to it form in the paint surface.
  • the measuring temperature is about 23 +/- 2 ° C and the humidity about 50%.
  • the excess sand is removed with a brush and determines the length of the pressure marks and the length of the sand trace.
  • the tack-free time is obtained by multiplying the length of the sand track by the speed of the funnel and the through-drying time by multiplying the length of the pressure track by the speed of the funnel.
  • Hardness PH pendulum hardness on galvanized steel based on DIN EN ISO 1522 / K ⁇ NIG method
  • Solvent resistance based on DIN 68860/68861 and DIN EN 12720. Table 1 :

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Epoxy Resins (AREA)

Abstract

L'invention concerne des compositions de résine époxy contenant : a) des résines époxy et b) au moins un dérivé de 2-oxo-[1,3] dioxolane de la formule (I), dans laquelle un ou deux des groupements R1 à R4 représentent un groupe organique électrophile ayant 1 à 20 atomes de carbone ou un hétéro-atome électrophile, les autres groupements R1 à R4 représentant indépendamment les uns des autres un atome hydrogène ou un groupe hydrocarbure ayant 1 à 20 atomes de carbone.
PCT/EP2012/069304 2011-10-04 2012-10-01 Compositions de résine époxy contenant un dérivé de 2-oxo-[1,3]dioxolane WO2013050311A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
EP12769403.2A EP2764033B1 (fr) 2011-10-04 2012-10-01 Compositions de résine époxy contenant un dérivé de 2-oxo-[1,3]dioxolane
DK12769403.2T DK2764033T3 (en) 2011-10-04 2012-10-01 EPOXIDHARPIKSSAMMENSÆTNINGER CONTAINING A 2-OXO [1,3] dioxolane

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP11183763 2011-10-04
EP11183763.9 2011-10-04

Publications (1)

Publication Number Publication Date
WO2013050311A1 true WO2013050311A1 (fr) 2013-04-11

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EP (1) EP2764033B1 (fr)
DK (1) DK2764033T3 (fr)
WO (1) WO2013050311A1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9062136B2 (en) 2012-03-29 2015-06-23 Basf Se Polymerizable alkylidene-1,3-dioxolane-2-one and use thereof
US9193862B2 (en) 2012-02-22 2015-11-24 Basf Se Blends for composite materials
WO2016169858A1 (fr) 2015-04-23 2016-10-27 Basf Se Carbonates cycliques

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3781379A (en) 1971-08-16 1973-12-25 Ford Motor Co Powdered coating compositions containing glycidyl methacrylate copolymers with anhydride crosslinking agents and flow control agent
DE2214650B2 (de) 1971-03-26 1975-04-30 Kansai Paint Co., Ltd., Amagasaki, Hyogo (Japan) Härtbare Acrylpulver-Beschlchtungsmasse
EP0001088A1 (fr) * 1977-09-05 1979-03-21 BASF Aktiengesellschaft Polymères contenant des groupes carbonates
DE2749576B2 (de) 1977-11-05 1979-08-16 Deutsche Gold- Und Silber-Scheideanstalt Vormals Roessler, 6000 Frankfurt Verfahren zur Herstellung eines Glycidylgruppen aufweisenden Acrylharzes und dessen Verwendung
EP0299420A2 (fr) 1987-07-16 1989-01-18 Ppg Industries, Inc. Polyanhydride modifiée comme durcisseur pour des revêtements sous forme de poudre à base de polyépoxyde
EP0656384A2 (fr) * 1993-11-02 1995-06-07 Hoechst Aktiengesellschaft Systèmes de polymères, procédé pour leur préparation et leur utilisation dans les encres
WO2010089264A1 (fr) * 2009-02-05 2010-08-12 Basf Se Procédé pour préparer des bicarbonates

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2214650B2 (de) 1971-03-26 1975-04-30 Kansai Paint Co., Ltd., Amagasaki, Hyogo (Japan) Härtbare Acrylpulver-Beschlchtungsmasse
US3781379A (en) 1971-08-16 1973-12-25 Ford Motor Co Powdered coating compositions containing glycidyl methacrylate copolymers with anhydride crosslinking agents and flow control agent
US4091048A (en) 1971-08-16 1978-05-23 Ford Motor Company Powder coating compositions containing glycidyl ester copolymers and organic carboxylic acid anhydride crosslinking agent
EP0001088A1 (fr) * 1977-09-05 1979-03-21 BASF Aktiengesellschaft Polymères contenant des groupes carbonates
DE2749576B2 (de) 1977-11-05 1979-08-16 Deutsche Gold- Und Silber-Scheideanstalt Vormals Roessler, 6000 Frankfurt Verfahren zur Herstellung eines Glycidylgruppen aufweisenden Acrylharzes und dessen Verwendung
EP0299420A2 (fr) 1987-07-16 1989-01-18 Ppg Industries, Inc. Polyanhydride modifiée comme durcisseur pour des revêtements sous forme de poudre à base de polyépoxyde
EP0656384A2 (fr) * 1993-11-02 1995-06-07 Hoechst Aktiengesellschaft Systèmes de polymères, procédé pour leur préparation et leur utilisation dans les encres
WO2010089264A1 (fr) * 2009-02-05 2010-08-12 Basf Se Procédé pour préparer des bicarbonates

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9193862B2 (en) 2012-02-22 2015-11-24 Basf Se Blends for composite materials
US9062136B2 (en) 2012-03-29 2015-06-23 Basf Se Polymerizable alkylidene-1,3-dioxolane-2-one and use thereof
WO2016169858A1 (fr) 2015-04-23 2016-10-27 Basf Se Carbonates cycliques
US10407534B2 (en) 2015-04-23 2019-09-10 Basf Se Cyclic carbonates

Also Published As

Publication number Publication date
DK2764033T3 (en) 2015-09-14
EP2764033B1 (fr) 2015-06-17
EP2764033A1 (fr) 2014-08-13

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